Triethylamine → tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 538734ノート

反応式

HRID 538734 の反応式
[CH:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.C([O-])(=O)C.[NH4+:19].C([N:22](CC)[CH2:23][CH3:24])C>>[NH:19]1[CH:24]=[CH:23][N:22]=[C:1]1[C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

参加物

4

反応物 3

HCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

生成物 1

HCID 49783269tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate収率 136.9%

反応条件

温度
140 °C

実験手順

A mixture of 4 (11.09 g, 25.3 mmol), ammonium acetate (29.25 g, 38.0 mmol) and triethylamine (38.45 g, 38.0 mmol) in xylenes (600 mL) in a sealed tube was stirred at 140° C. for 2 h. After being cooled, the reaction mixture was transferred into a flask and concentrated to dryness. The residue was partitioned between chloroform and H2O, and the organic layer was washed with H2O and concentrated. The crude product was purified by silica gel column chromatography (NH4OH/acetonitrile/ethyl acetate: 1/8/100=(v/v/v)) to afford 5 (8.22 g, 75% yield) as a white solid. LC-MS (ESI): m/z 420.1 (M+H)+.

後処理

  1. temperatureAfter being cooled
  2. customthe reaction mixture was transferred into a flask
  3. concentrationconcentrated to dryness
  4. customThe residue was partitioned between chloroform and H2O
  5. washthe organic layer was washed with H2O
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography (NH4OH/acetonitrile/ethyl acetate: 1/8/100=(v/v/v))

出典と根拠

ORDレコード
ord-c8e851cf96fe452094a34537bcb3aecf
出典データセット
uspto-grants-2014_10
特許番号
US08865756B2

反応ノート

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